Consumer photo editing is on the rise due at least in part to wide availability of the mobile phones, tablets, and other portable devices that include cameras and are powerful enough to support image editing software. A variety of different editing operations may be applied to process an image. One example is a cropping operation in which a sub-region of a particular image may be selected to produce a “cropped” image. For instance, cropping may be performed by users to remove unwanted objects or individuals from photos taken “on-the-go” before sharing the photos via messaging, social networks, photo sharing sites, and so forth. Some traditional photo editing applications provide largely manual cropping workflows in which a user may have to perform multiple steps to select a crop boundary, resize the canvas, and backfill content in order to produce a visually pleasant output image. Other more rudimentary cropping tools may be used to create cropped version of images that adversely alter the pixel resolution, image size, aspect ratio, and so forth. Accordingly, it may be difficult and frustrating for some users, such as un-savvy consumers, to utilize traditional cropping workflows for creating cropped photos, particularly in relation to on-the-go sharing scenarios.